The Design,synthesis And Functionalization Of Organic Small Molecule Basing On Bis-lactam Dyes

For a century the chemists are persistently pursuing the different cyclic structures,as this kind of structures not only exhibit unrivalled beauty,but also bring dramatical different properties to the acyclic(linear)analogues.Because the cyclic structures have potential advantages and promising application.For example,the cycles have well-defined internal cavities that can be the supramolecular hosts for the investigation of noncovalent interactions by introducing a guest molecule.On the other hand they also can be efficient fluorescence,Recently years,cyclic pi-conjugated systems are also emerging as efficacious materials in organic photovoltaics(OPVs).Chiral molecules are widely applied in numerous fields such as chiral recognition,enantioselective catalysis.As well as in nonlinear optics and as molecular switches.Although a larger number of functional chiral pi-system have been synthesized,most of them are not conformationally stable due to the dynamic racemization process.Diketopyrrolopyrrole(DPPs)have attracted great attention for their wide of applications,for example,as chromophores for supramolecular system,as useful building blocks to construct versatile organic semiconductors for organic field-effect transistor and solar cells.Their easy accessibility,electron-deficient properties of the bislactams,and high molar absorptivity in the visible region.However,to our knowledge,a conformational chirality of DPPs are unprecedented to date,not to mention conformationally ambient stable enantio-pure DPPs.Since the design and synthesis of chiral rings with cavities and composed of the functional dyes remains challenging.Herein,we have made efforts to achieve a series of different length of flexible alkylene linked DPPs rings and further to achieve conformationally stable and atropo-enantiomerically pure DPPs.Their solid states properties have been investigated systemically.In this paper,with pyrropyrrole dione as the central nucleus,the alkyl chain and alkoxyl-linked small molecular structure were designed,and the dithiophene pyrropyrrole dione ring [9,9,11] was used as the central molecular structure,and the effects of different lengths of flexible alkyl chain and alkoxyl chain,thiophene and pyridine substituent groups on ring molecules and chiral structures were compared.The chiral enantiomer structure with pure and stable configuration was obtained by high performance liquid chromatography(HPLC).The structure was characterized by ultraviolet absorption spectrum,fluorescence spectrum,electrochemical analysis,thermodynamic analysis,circular dichroism and single crystal structure.